2-Aminothiazole

Chemical compound From Wikipedia, the free encyclopedia

2-Aminothiazole is a heterocyclic amine featuring a thiazole core. It can also be considered a cyclic isothiourea. It possesses an odor similar to pyridine and is soluble in water, alcohols and diethyl ether. 2-Aminothiazole itself is mainly of academic interest, with few exceptions. It is a precursor to a sulfathiazole ("sulfa drugs"). 2-Aminothiazole can be used as a thyroid inhibitor in the treatment of hyperthyroidism.[2]

Quick facts Names, Identifiers ...
2-Aminothiazole
Skeletal formula of aminothiazole
Space-filling model of the aminothiazole molecule
Names
Preferred IUPAC name
1,3-Thiazol-2-amine
Other names
2-Thiazolamine, Aminothiazole, 2-Thiazylamine, Basedol, 2-Thiazolylamine, 4-Thiazolin-2-onimine, 2-Amino-1,3-thiazole, Abadole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.284 Edit this at Wikidata
EC Number
  • 202-511-6
KEGG
UNII
  • InChI=1S/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5) checkY
    Key: RAIPHJJURHTUIC-UHFFFAOYSA-N checkY
  • InChI=1/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5)
    Key: RAIPHJJURHTUIC-UHFFFAOYAZ
  • c1csc(n1)N
Properties
C3H4N2S
Molar mass 100.14 g·mol−1
Appearance Light yellow crystals
Melting point 86 to 89 °C (187 to 192 °F; 359 to 362 K)
Boiling point 117 °C (243 °F; 390 K) (20 hPa)
100 g/L (20 °C)
−56.0·10−6 cm3/mol
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H302, H319
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
600 °C (1,112 °F; 873 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
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2-Aminothiazole is prepared from paraldehyde, thiourea, and sulfuryl chloride.[3]

2-Aminothiazoles

Like the parent, 2-aminothiazoles are often produced by the condensation of thiourea and an alpha-halo ketone.[4][5][6]

Hantsch Thiazole Synthesis
Hantsch Thiazole Synthesis

In an adaptation of the Robinson-Gabriel synthesis, a 2-acylamino-ketone reacts with phosphorus pentasulfide.

Applications

Synthetic aminothiazoles - compounds containing the parent 2-aminothiazole as a subunit - are used in medicinal chemistry. Some examples are abafungin, acotiamide, amiphenazole, amthamine, avatrombopag, aztreonam, cefepime, cefixime, ceftizoxime, ceftiofur, ceftibuten, cefpirome, famotidine, meloxicam, and pramipexole.[7][8]

See a related compound called 2-Amino-2-thiazoline [1779-81-3].[9]

References

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